RU2012134548A - Heterocyclic carboxylic acid derivatives having a 2,5-substituted oxazolopyrimidine ring - Google Patents

Abstract

1. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio or its physiologically acceptable salt, or physiologically acceptable solvate of any of them, where A is selected from NH, O and S; X is selected from (C-C) -alkanediyl, (C-C) -alkendiyl, (C-C) -alkindiyl, (CC) -cycloalkanediyl and (CC) -alkanediyl-oxy, which are all optionally substituted with one or more identical or different substituents selected from fluorine and hydroxy, where the oxygen atom of the (CC) alkanediyl hydroxy group is bonded to the group R; Y is it has a 4-7 membered, saturated or partially unsaturated, monocyclic or bicyclic heterocycle which, in addition to the ring nitrogen atom shown in formula I, contains 0, 1, 2 or 3 identical or different ring heteroatoms selected from N, O and S, where one or two additional ring nitrogen atoms can carry a hydrogen atom or a (CC) -alkyl substituent and one of the ring sulfur atoms can carry one or two oxo groups, and where the heterocycle is optionally substituted on one or more ring carbon atoms, identical or different personal (CC) -alkyl substituents; R is selected from hydrogen, (CC) -alkyl and (C-C) -cycloalkyl-CH-, where z is selected from 0, 1 and 2; R is selected from phenylene and a divalent aromatic residue 5-6- a monocyclic heterocycle containing 1, 2 or 3 identical or different ring heteroatoms selected from N, O and S, where one of the ring nitrogen atoms may carry a hydrogen atom or an R substituent, and where the phenylene and divalent aromatic heterocycle are optionally substituted on one or more carbon atoms of the ring are identical or

Claims (21)

1. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio or its physiologically acceptable salt, or physiologically acceptable solvate of any of them,

where A is selected from NH, O and S; X is selected from (C ₁ -C ₆ ) -alkanediyl, (C ₂ -C ₆ ) -alkendiyl, (C ₂ -C ₆ ) -alkindiyl, (C ₃ -C ₇ ) -cycloalkanediyl and (C ₁ -C ₆ ) -alkanediyl-oxy, which are all optionally substituted with one or more identical or different substituents selected from fluorine and hydroxy, where the oxygen atom of a (C ₁ -C ₆ ) -alkanediyl-hydroxy group is attached to the group R ² ; Y represents a 4-7 membered, saturated or partially unsaturated, monocyclic or bicyclic heterocycle which, in addition to the ring nitrogen atom shown in formula I, contains 0, 1, 2 or 3 identical or different ring heteroatoms selected from N, O and S, where one or two additional ring nitrogen atoms can carry a hydrogen atom or a (C ₁ -C ₄ ) -alkyl substituent and one of the ring sulfur atoms can carry one or two oxo groups, and where the heterocycle is optionally substituted on one or more atoms carbon rings ident egg or various (C ₁ -C ₄ ) -alkyl substituents; R ^{1 is} selected from hydrogen, (C ₁ -C ₄ ) -alkyl and (C ₃ -C ₇ ) -cycloalkyl-C _z H _2z -, where z is selected from 0, 1 and 2; R ^{2 is} selected from phenylene and a divalent residue of an aromatic 5-6 membered monocyclic heterocycle that contains 1, 2 or 3 identical or different ring heteroatoms selected from N, O and S, where one of the ring nitrogen atoms can carry a hydrogen atom or a substituent R ²¹ , and where phenylene and a divalent aromatic heterocycle residue are optionally substituted on the one or more ring carbon atoms with identical or different R ²² substituents; R ^{3 is} selected from (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₃ -C ₇ ) -cycloalkyl-C _u H _2u - and Het-C _v H _2v -, wherein u and v are chosen from 1 and 2, or R ³ represents the residue of a saturated or unsaturated, 3-10-membered, monocyclic or bicyclic ring which comprises 0, 1, 2, 3 or 4 identical or various ring heteroatoms selected from N, O and S, where one or two ring nitrogen atoms can carry a hydrogen atom or a (C ₁ -C ₄ ) alkyl substituent and one or two ring sulfur atoms can carry one or two oxo groups, and where the remainder of the ring is optionally substituted on identical or different R ³¹ substituents on one or more carbon atoms of the ring; R ^{21 is} selected from (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl-C _w H _2w - and hydroxy, where w is selected from 0, 1 and 2; R ^{22 is} selected from halogen, hydroxy, (C ₁ -C ₄ ) -alkyl-, (C ₁ -C ₄ ) -alkyloxy, (C ₁ -C ₄ ) -alkyl-S (O) _m -, amino, nitro, cyano, hydroxycarbonyl, (C ₁ -C ₄ ) -alkyloxycarbonyl, aminocarbonyl and aminosulfonyl; R ^{31 is} selected from halogen, (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl, hydroxy, (C ₁ -C ₄ ) -alkyloxy, oxo, (C ₁ -C ₄ ) -alkyl- S (O) _m -, amino, (C ₁ -C ₄ ) -alkylamino, di ((C ₁ -C ₄ ) -alkyl) amino, (C ₁ -C ₄ ) -alkylcarbonylamino, (C ₁ -C ₄ ) -alkilsulfonilamino, nitro, cyano, (C ₁ -C ₄₎ -alkylcarbonyl, aminosulfonyl, (C ₁ -C ₄₎ -alkilaminosulfonila and di ((C ₁ -C ₄₎ -alkyl) aminosulfonyl; Het represents a residue of a saturated 4-7 membered monocyclic heterocycle that contains 1 or 2 identical or different ring heteroatoms selected from N, O and S, and which is attached via a carbon atom of the ring, where the heterocycle residue is optionally substituted with one or more identical or various substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; m is selected from 0, 1 and 2, where all numbers m are independent of each other; where all cycloalkyl and cycloalkanediyl groups, independently of one another and independently of any other substituents, are optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; where all the groups alkyl, alkanediyl, C _u H _2u , C _v H _2v , C _w H _2w , C _z H _2z , alkenyl, alkenediyl, alkynyl and alkindiyl are independently of one another and independently of any other substituents are optionally substituted with one or more fluorine substituents. 2. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of claim 1, wherein A is selected from O and S. 3. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of claim 1, wherein X is selected from (C ₁ -C ₆ ) alkanediyl , (C ₂ -C ₆ ) -alkenediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy. 4. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of claim 1, wherein Y is a 4-7 membered saturated monocyclic or bicyclic heterocycle which, in addition to the ring nitrogen atom shown in Formula I, contains 0 or 1 ring heteroatom selected from N, O and S, where the additional ring nitrogen atom can carry a hydrogen atom or a (C ₁ -C ₄ ) alkyl substituent and the sulfur atom of the ring can carry one or two oxo groups, and wherein the heterocycle is optionally substituted on the one or more ring carbon atoms by identical or different (C ₁ -C ₄ ) alkyl substituents. 5. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of claim 1, wherein R ^{2 is} selected from phenylene and pyridinediyl, where phenylene and pyridinediyl are optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents. 6. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them according to claim 1, where R ^{3 is} selected from (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl-C _u H _2u - and Het-C _v H _2v -, where u and v are selected from 1 and 2, or R ³ means the residue of a saturated or unsaturated, 3-10 membered, monocyclic or bicyclic ring that contains O, 1 or 2 identical or different ring heteroatoms selected from N, O and S, where one or two ring nitrogen atoms can carry a hydrogen atom or (C ₁ -C ₄₎ -alkyl substituent and one of the ring sulfur atoms can carry one or two oxo groups, and wherein the residue of the ring is optionally substituted on one or more carbon atoms to ltsa identical or different substituents R ^31; Het means a residue of a saturated 4-6 membered monocyclic heterocycle that contains 1 ring heteroatom selected from N, O and S, and which is linked via a ring carbon atom, where the heterocycle residue is optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl. 7. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any one of one or more of claims 1 to 6, where A is selected from O and S; X is selected from (C ₁ -C ₆ ) -alkanediyl, (C ₂ -C ₆ ) -alkenediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy; Y represents a 4-7 membered saturated monocyclic or bicyclic heterocycle which, in addition to the ring nitrogen atom shown in formula I, contains 0 or 1 ring heteroatom selected from N, O and S, where the additional ring nitrogen atom can carry a hydrogen atom or a (C ₁ -C ₄ ) alkyl substituent and a ring sulfur atom may carry one or two oxo groups, and wherein the heterocycle is optionally substituted on the one or more ring carbon atoms by identical or different (C ₁ -C ₄ ) alkyl substituents; R ^{2 is} selected from phenylene and pyridinediyl, where phenylene and pyridinediyl are optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents; R ^{3 is} selected from (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl-C _u H _2u - and Het-C _v H _2v -, where u and v are selected from 1 and 2, or R ³ means the remainder of a saturated or unsaturated 3-10 membered monocyclic or bicyclic ring which contains O, 1 or 2 identical or different ring heteroatoms selected from N, O and S, where one or two ring nitrogen atoms can carry a hydrogen atom or ( A C ₁ -C ₄ ) -alkyl substituent and one of the ring sulfur atoms may carry one or two oxo groups, and where the remainder of the ring is optionally substituted on one or more carbon atoms lts identical or different substituents R ³¹ ; Het means a residue of a saturated 4-6 membered monocyclic heterocycle that contains 1 ring heteroatom selected from N, O and S, and which is linked via a ring carbon atom, where the heterocycle residue is optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl. 8. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any one of claim 1, where A is selected from O and S; X is selected from (C ₁ -C ₆ ) -alkanediyl, (C ₂ -C ₆ ) -alkenediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy; Y represents a 4-7 membered saturated monocyclic or bicyclic heterocycle which, in addition to the ring nitrogen atom shown in formula I, contains 0 or 1 ring heteroatom selected from N, O and S, where the additional ring nitrogen atom can carry a hydrogen atom or a (C ₁ -C ₄ ) alkyl substituent and a ring sulfur atom may carry one or two oxo groups, and wherein the heterocycle is optionally substituted on the one or more ring carbon atoms by identical or different (C ₁ -C ₄ ) alkyl substituents; R ^{2 is} selected from phenylene and pyridinediyl, where phenylene and pyridinediyl are optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents; R ^{3 is} selected from (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl-C _u H _2u - and Het-C _v H _2v -, where u and v are selected from 1 and 2, or R ³ means the remainder of a saturated or unsaturated 3-10 membered monocyclic or bicyclic ring which contains O, 1 or 2 identical or different ring heteroatoms selected from N, O and S, where one or two ring nitrogen atoms can carry a hydrogen atom or ( C ₁ -C ₄₎ -alkyl substituent and one of the ring sulfur atoms can carry one or two oxo groups, and wherein the residue of the ring is optionally substituted on one or more carbon atoms to ltsa identical or different substituents R ^31; Het means a residue of a saturated 4-6 membered monocyclic heterocycle that contains 1 ring heteroatom selected from N, O and S, and which is linked via a ring carbon atom, where the heterocycle residue is optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl. 9. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them according to one of claims 1 to 6 or 8, where A means O; X is selected from (C ₁ -C ₆ ) -alkanediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy; Y represents a 4-6 membered saturated monocyclic heterocycle that does not contain additional ring heteroatoms in addition to the nitrogen atom of the ring shown in Formula I, where the ring is optionally substituted on the one or more ring carbon atoms identical or different (C ₁ -C ₄ ) -alkyl substituents; R ¹ selected from hydrogen and (C ₁ -C ₄ ) -alkyl; R ² represents phenylene, which is optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents; R ^{3 is} selected from (C ₃ -C ₇ ) -cycloalkyl-C _u H _2u - and Het-C _v H _2v -, where u and v are selected from 1 and 2, or R ³ means a residue of saturated or unsaturated 3-7- a monocyclic or bicyclic ring member which contains 0, 1 or 2 identical or different ring heteroatoms selected from N, O and S, where one or two ring nitrogen atoms can carry a hydrogen atom or a (C ₁ -C ₄ ) alkyl substituent and one of the ring sulfur atoms may carry one or two oxo groups, and where the remainder of the ring is optionally substituted on one or more carbon atoms, the rings are identical mi or various substituents R ³¹ ; R ^{22 is} selected from halogen, hydroxy, (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ ) alkyloxy; R ³¹ is selected from halo, (C ₁ -C ₄₎ -alkyl, (C ₃ -C ₇₎ -cycloalkyl, hydroxy and (C ₁ -C ₄₎ -alkyloxy; Het means a residue of a saturated 4-6 membered monocyclic heterocycle that contains 1 ring heteroatom selected from O and S, and which is linked via a ring carbon atom, where the heterocycle residue is optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; where all cycloalkyl groups independently and independently of any other substituents are optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; where all the alkyl, alkanediyl, C _u H _2u and C _v H _2v groups, independently of one another and independently of any other substituents, are optionally substituted with one or more fluorine substituents. 10. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any one of claim 1, where A means O; X is selected from (C ₁ -C ₆ ) -alkanediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy; Y represents a 4-6 membered saturated monocyclic heterocycle that does not contain additional ring heteroatoms in addition to the nitrogen atom of the ring shown in Formula I, where the ring is optionally substituted on the one or more ring carbon atoms identical or different (C ₁ -C ₄ ) -alkyl substituents; R ¹ is selected from hydrogen and (C ₁ -C ₄₎ -alkyl; R ² represents phenylene, which is optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents; R ^{3 is} selected from (C ₃ -C ₇ ) -cycloalkyl-C _u H _2u - and Het-C _v H _2v -, where u and v are selected from 1 and 2, or R ³ means a residue of saturated or unsaturated 3-7- a monocyclic or bicyclic ring member which contains 0, 1 or 2 identical or different ring heteroatoms selected from N, O and S, where one or two ring nitrogen atoms can carry a hydrogen atom or a (C ₁ -C ₄ ) alkyl substituent and one of the ring sulfur atoms may carry one or two oxo groups, and where the remainder of the ring is optionally substituted on one or more ring carbon atoms is identical E or different substituents R ^31; R ^{22 is} selected from halogen, hydroxy, (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ ) alkyloxy; R ^{31 is} selected from halogen, (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl, hydroxy and (C ₁ -C ₄ ) -alkyloxy; Het means a residue of a saturated 4-6 membered monocyclic heterocycle that contains 1 ring heteroatom selected from O and S, and which is linked via a ring carbon atom, where the heterocycle residue is optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; where all cycloalkyl groups independently and independently of any other substituents are optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; wherein all alkyl, alkanediyl, C _u H _2u and C _v H _2v groups independently of each other and independently of any other substituents are optionally substituted with one or more fluoro substituents. 11. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them according to one of claims 1 to 6, 8 or 10, where A represents O; X is selected from (C ₁ -C ₆ ) -alkanediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy; Y represents a 4-6 membered saturated monocyclic heterocycle that does not contain additional ring heteroatoms in addition to the nitrogen atom of the ring shown in Formula I, where the ring is optionally substituted on the one or more ring carbon atoms identical or different (C ₁ -C ₄ ) -alkyl substituents; R ¹ selected from hydrogen and (C ₁ -C ₄ ) -alkyl; R ² represents phenylene, which is optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents; R ³ means the residue of a saturated or unsaturated 3-7 membered monocyclic ring which contains 0 or 1 ring heteroatom selected from N, O and S, where the ring nitrogen atom may carry a hydrogen atom or a (C ₁ -C ₄ ) -alkyl substituent and the ring sulfur atom may carry one or two oxo groups, and where the ring residue is optionally substituted on the one or more ring carbon atoms by identical or different R ³¹ substituents; R ^{22 is} selected from halogen, hydroxy, (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ ) alkyloxy; R ^{31 is} selected from halogen, (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl, hydroxy and (C ₁ -C ₄ ) -alkyloxy; where all cycloalkyl groups independently and independently of any other substituents are optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; where all the alkyl, alkanediyl, C _u H _2u and C _v H _2v groups, independently of one another and independently of any other substituents, are optionally substituted with one or more fluorine substituents. 12. The compound of formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any one of claim 1, where A represents O; X is selected from (C ₁ -C ₆ ) -alkanediyl and (C ₁ -C ₆ ) -alkanediyl-hydroxy; Y represents a 4-6 membered saturated monocyclic heterocycle that does not contain additional ring heteroatoms in addition to the nitrogen atom of the ring shown in Formula I, where the ring is optionally substituted on the one or more ring carbon atoms identical or different (C ₁ -C ₄ ) -alkyl substituents; R ¹ selected from hydrogen and (C ₁ -C ₄ ) -alkyl; R ² represents phenylene, which is optionally substituted on one or more ring carbon atoms with identical or different R ²² substituents; R ³ means the residue of a saturated or unsaturated 3-7 membered monocyclic ring which contains 0 or 1 ring heteroatom selected from N, O and S, where the ring nitrogen atom may carry a hydrogen atom or a (C ₁ -C ₄ ) -alkyl substituent and the ring sulfur atom may carry one or two oxo groups, and where the ring residue is optionally substituted on the one or more ring carbon atoms by identical or different R ³¹ substituents; R ^{22 is} selected from halogen, hydroxy, (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ ) alkyloxy; R ^{31 is} selected from halogen, (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl, hydroxy and (C ₁ -C ₄ ) -alkyloxy; where all cycloalkyl groups independently and independently of any other substituents are optionally substituted with one or more identical or different substituents selected from fluorine and (C ₁ -C ₄ ) -alkyl; where all the alkyl, alkanediyl, C _u H _2u and C _v H _2v groups, independently of one another and independently of any other substituents, are optionally substituted with one or more fluorine substituents. 13. The compound of formula I or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them according to one of claims 1 to 6, 8, 10 or 12, selected from the following: (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] -2,6-dimethyl-phenoxy} acetyl) pyrrolidine -2-carboxylic acid (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] -2,6-dimethyl-phenoxy} propionyl) pyrrolidine -2-carboxylic acid (S) -1 - ((E) -3- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenyl} acryloyl) pyrrolidin-2- carboxylic acid (S) -1- (3- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenyl} propionyl) pyrrolidine-2-carboxylic acid, (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] -2-methyl-phenoxy} acetyl) pyrrolidin-2 -carboxylic acid (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenoxy} acetyl) pyrrolidine-2-carboxylic acid, 1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenoxy} acetyl) piperidine-4-carboxylic acid and (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenoxy} propionyl) pyrrolidine-2-carboxylic acid. 14. The compound of formula I or a physiologically acceptable salt, it, or a physiologically acceptable solvate of any of them according to claim 1, selected from the following: (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] -2,6-dimethyl-phenoxy} acetyl) pyrrolidine -2-carboxylic acid (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] -2,6-dimethyl-phenoxy} propionyl) pyrrolidine -2-carboxylic acid (S) -1 - ((E) -3- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenyl} acryloyl) pyrrolidin-2- carboxylic acid (S) -1- (3- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenyl} propionyl) pyrrolidine-2-carboxylic acid, (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] -2-methyl-phenoxy} acetyl) pyrrolidin-2 -carboxylic acid (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenoxy} acetyl) pyrrolidine-2-carboxylic acid, 1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenoxy} acetyl) piperidine-4-carboxylic acid and (S) -1- (2- {4- [5- (2-fluoro-phenoxy) -oxazolo [5,4-d] pyrimidin-2-yl] phenoxy} propionyl) pyrrolidine-2-carboxylic acid. 15. A method of obtaining a compound of formula I according to any one of claims 1 to 14, comprising reacting a compound of formula II with a compound of formula III,

where groups A, X, Y, R ¹ , R ² and R ³ in the compounds of formulas II and III have the meanings indicated for the compounds of formula I, and further functional groups can be represented in a protected form or in the form of precursor groups and L ¹ means a halogen atom or a group of the formula -S (O) -Alk or -S (O) ₂ -Alk, where Alk is (C ₁ -C ₄ ) -alkyl. 16. A pharmaceutical composition comprising at least one compound of formula I according to any one of claims 1 to 14 or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them and a pharmaceutically acceptable carrier. 17. The compound of formula I according to any one of claims 1 to 6, 8, 10, 12 or 14, or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them for use as a pharmaceutical. 18. The compound of formula I according to any one of claims 1 to 6, 8, 10, 12 or 14, or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them for the treatment of wound healing disorders. 19. The compound of formula I according to any one of claims 1 to 6, 8, 10, 12 or 14, or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them for wound healing. 20. The compound of formula I according to any one of claims 1 to 6, 8, 10, 12 or 14, or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them for wound healing in diabetics. 21. The compound of formula I according to any one of claims 1 to 6, 8, 10, 12 or 14, or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them for the treatment of diabetic foot syndrome.